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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL490
CHEMBL490
Compound Name PAROXETINE
ChEMBL Synonyms PAROXETINE HYDROCHLORIDE | BRL-29060 | Paxil cr | Pexeva | Paroxetine Hydrochloride Hemihydrate | PEXEVA | PAXIL | PAROXETINE MESYLATE | PAXIL [AS HYDROCHLORIDE] | PAROXETINE | POT.MES | Paxil | BRL 29060 | [3H]-Paroxetine
Max Phase 4 (Approved)
Trade Names PAXIL | PEXEVA | Paroxetine hydrochloride | Paxil cr | PAXIL [AS HYDROCHLORIDE]
Molecular Formula C19H20FNO3

Additional synonyms for CHEMBL490 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Fc1ccc(cc1)[C@@H]2CCNC[C@H]2COc3ccc4OCOc4c3
Standard InChI InChI=1S/C19H20FNO3/c20-15-3-1-13(2-4-15)17-7-8-21-10-14(17) ...
Download InChI
Standard InChI Key AHOUBRCZNHFOSL-YOEHRIQHSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Drugs for Neglected Diseases Initiative (DNDi)
  • Gene Expression Atlas Compounds
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL490

Molecule Features

CHEMBL490 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Serotonin transporter inhibitor Serotonin transporter DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
STRESS DISORDERS, POST-TRAUMATICD013313EFO:0001358POST-TRAUMATIC STRESS DISORDER4ClinicalTrials
DEPRESSIVE DISORDERD003866EFO:0003761UNIPOLAR DEPRESSION4ClinicalTrials
ClinicalTrials
ATC
FIBROMYALGIAD005356EFO:0005687FIBROMYALGIA1ClinicalTrials
MENOPAUSED008593EFO:0003922MENOPAUSE3ClinicalTrials
ANXIETYD001007EFO:0005230ANXIETY3ClinicalTrials
PREMATURE EJACULATIOND061686HP:0012876PREMATURE EJACULATION3ClinicalTrials

Clinical Data

ClinicalTrials.gov PAROXETINE
The Cochrane Collaboration PAROXETINE

Metabolites for CHEMBL490

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL490. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL228 Serotonin transporter Homo sapiens 1.000
CHEMBL313 Serotonin transporter Rattus norvegicus 1.000
CHEMBL222 Norepinephrine transporter Homo sapiens 1.000
CHEMBL304 Norepinephrine transporter Rattus norvegicus 0.999
CHEMBL338 Dopamine transporter Rattus norvegicus 0.997
CHEMBL238 Dopamine transporter Homo sapiens 0.992
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.938
CHEMBL4980 Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus 0.844
CHEMBL6184 Transporter Rattus norvegicus 0.502
CHEMBL1833 Serotonin 2b (5-HT2b) receptor Homo sapiens 0.489
CHEMBL240 HERG Homo sapiens 0.413
CHEMBL1916 Alpha-2c adrenergic receptor Homo sapiens 0.327
CHEMBL340 Cytochrome P450 3A4 Homo sapiens 0.200



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL228 Serotonin transporter Homo sapiens 1.000
CHEMBL313 Serotonin transporter Rattus norvegicus 1.000
CHEMBL222 Norepinephrine transporter Homo sapiens 1.000
CHEMBL304 Norepinephrine transporter Rattus norvegicus 1.000
CHEMBL238 Dopamine transporter Homo sapiens 1.000
CHEMBL338 Dopamine transporter Rattus norvegicus 0.999
CHEMBL240 HERG Homo sapiens 0.975
CHEMBL6184 Transporter Rattus norvegicus 0.872
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.863
CHEMBL1916 Alpha-2c adrenergic receptor Homo sapiens 0.847
CHEMBL1833 Serotonin 2b (5-HT2b) receptor Homo sapiens 0.809
CHEMBL4980 Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus 0.800
CHEMBL4481 Nitric oxide synthase, inducible Homo sapiens 0.523
CHEMBL1867 Alpha-2a adrenergic receptor Homo sapiens 0.397
CHEMBL344 Melanin-concentrating hormone receptor 1 Homo sapiens 0.215

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
329.4 329.1427 3.23 4 39.72 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 1 0 4 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 9.68 3.7 1.48 2 24 0.94

Structural Alerts

There are 1 structural alerts for CHEMBL490. To view alerts please click here.

Compound Cross References

ATC N - NERVOUS SYSTEM
N06 - PSYCHOANALEPTICS
N06A - ANTIDEPRESSANTS
N06AB - Selective serotonin reuptake inhibitors
N06AB05 - paroxetine

ChemSpider ChemSpider:AHOUBRCZNHFOSL-YOEHRIQHSA-N
DailyMed paroxetine hydrochloride paroxetine mesylate
PubChem SID: 144206674 SID: 170465075 SID: 26752262 SID: 29215051 SID: 50104978 SID: 50104979 SID: 50104980 SID: 50104981 SID: 90341371
Wikipedia Paroxetine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL490



ACToR 110429-35-1 61869-08-7
Atlas paroxetine
BindingDB 50331515 22416
Brenda 75641 145977 36984
ChEBI 7936
DrugBank DB00715
DrugCentral 2068
eMolecules 1935652
EPA CompTox Dashboard DTXSID3023425
FDA SRS 41VRH5220H
Guide to Pharmacology 4790
Human Metabolome Database HMDB14853
IBM Patent System BA9CB78987006F7DD38940BBB3C63F01
KEGG Ligand C07415
LINCS LSM-2843
Nikkaji J259.859K
PDBe 8PR
PharmGKB PA450801
PubChem 43815
PubChem: Drugs of the Future 12013591
PubChem: Thomson Pharma 14924270 14850948
SureChEMBL SCHEMBL27799
ZINC ZINC000000527386

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/AHOUBRCZNHFOSL-YOEHRIQHSA-N spacer
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